


A Gentlemen's Agreement

by Hunter Stu (stunudo)



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Kink Series, M/M, Masturbation, Oral Sex, Phone Sex, Public Sex, Slash AU - Freeform, mlm
Language: English
Status: In-Progress
Published: 2020-02-23
Updated: 2021-01-20
Packaged: 2021-02-26 13:17:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 16,299
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22870264
Author URL: https://archiveofourown.org/users/stunudo/pseuds/Hunter%20Stu
Summary: Written for:  Tumblr user thoughtslikeaminefield birthday challenge thingy & SpnkinkbingoDean could use a distraction, luckily a few stores are still open. Benny helps him find more than he was looking for. Follow Dean as he navigates a sudden and intense relationship with Benny. Along the way he has to navigate those he loves from discovering his hidden sexuality without losing the best thing that ever happened to him. Can Dean be himself? Will Benny be able to be patient enough to wait until he's ready?Warnings: 18+ only. Mirrors. Unprofessional behavior. Consent is key. Fellatio. Public Sex. Internalized Bi-phobia. Masturbation. Sexting. Phone sex. Dirty talk. Hand jobs. Oral sex. Anal Sex. Rimming. Docking.
Relationships: Benny Lafitte/Dean Winchester
Comments: 11
Kudos: 12
Collections: SPN Kink Bingo 2020





	1. The Night Shift

Dean Winchester was a reluctant shopper. Not because he disliked the activity, but because he tended to feel a bit guilty when spending money on himself. Growing up all extra cash went to necessities and now that he had a healthy cushion in his bank account and last weekend’s tips burning a hole in his wallet; he found himself wandering through the outdated mall alone and uninspired. Maybe he should just buy something for Sam, save it for his birthday. Thinking of his overly educated little brother gave him more ideas than his own passing fancies.

Dean distracted himself walking through the crude novelty shop with the cackling horror movie figurines and abundant pop culture-related magnets. How some businesses stuck around after the decline of the flagship department stores, he’d never know. He bought a few shot glasses for his coworkers’ amusement and thanked the stoned clerk with a commiserating nod. The next shop down was a western style leather shop, the wood and skins merged into an enchanting aroma that tickled Dean with something between comfort and memory.

He’d always wanted a jacket made just for him, remembering the ill-fitted one of his dad’s he’d stolen in high school when all his friends were decked out in jean jackets and flannels. Couldn’t hurt to browse, Dean checked his watch: quarter to nine. He reminded himself not to be that customer and sauntered into the seemingly empty store, boots hitting the repurposed boards with soft thuds. The opening wall was covered in satchels and saddle bags, each one handcrafted and unique. The stains of the leather spanning every earth tone imaginable. Dean breathed deep through his nose, grazing his fingers over the first rack of jackets, enjoying the array of textures as he continued his search deeper into the store.

A gentle tapping sounded from a backroom in the corner, opposite the fitting rooms, reminding Dean that he was a guest in the cavernous space. The employee’s efforts must have been enthralling, because Dean was sure there had been an electronic welcome chime when he passed through the propped open door. He should probably comeback when it wasn’t closing time, when he had more of an idea what he was looking for. Just as he turned to go a smooth voice reached across the room and held him firm.

“Can I help you find anything?” The man drawled out an offer of help.

Dean spun, deft and breezy. “Just looking for now. Thanks, though, thinking I’ll come back, don’t want to keep you.”

Dean took in the shopkeeper, a burly guy with a precise goatee, broad chest fitted in a vest so seamless Dean would have guessed it was from a tailored three-piece suit and not cowhide. He had blue eyes that sparkled amidst their dark surroundings. A genuine smile perched on his welcoming face.

“It’s no bother. I’m just working on some new designs; they’re not going anywhere. What are you in the market for?”

“Looking for a jacket, but I have no clue what kind,” Dean said apologetically. The shopkeeper stepped closer, getting a read on Dean from his boots up his bowed legs, to the belt on his trip hips and over his layered button down. Dean’s entire body tensed with the appraisal.

“’s alright. Have a look around, name’s Benny if you find something you like–,” he said softly now that they stood closer. “Or have any questions.”

“Thanks.” Dean swallowed, shoving his hands in the pockets of his jeans, a blush burning down the back of his neck, but he didn’t break eye contact.

Benny backed away with a simple gesture, presenting the whole of his inventory for Dean’s discernment. A mischievous smirk lingered before either looked away. Dean inhaled and tried to narrow down his search, but Benny’s presence was holding half of his attention, even from across the room. His watch read 8:52, he started to worry he was wasting both their time when he spotted it. A dark biker jacket with dual breast pockets, a belt hung loosely at the neck of the headless mannequin, all trimmed in zippers and buttons. It screamed danger and oozed sex. Dean suddenly needed to do both of those things.

“Uh, got any more of these?” Dean called over his shoulder.

Benny strolled out from behind the register, head cocked as he looked from Dean to the display and back again. “Why don’t you try it on? Looks like it just might be made for you.”

“Yeah? Hell, why not?” Dean chuckled, carefully unfurling the hems from the canvas bust. He shrugged into the sleeves, bowing his elbows before straightening the material down his chest.

Benny whistled appreciatively. “Well now, gone on, go have a look.” He nodded Dean back to the triptych of mirrors outside the changing room. The leatherworker loved to see his work on such a fine canvas after all. He followed the customer at a leisurely pace, arms folded over his chest as the younger man primped.

Vanity and excitement brightened Dean’s face with an indulgent grin. “Man, this is something.”

He stole a glance at Benny in the mirror, large biceps pushing the confines of his shirt sleeves, cuffed at the elbow. He wore dark jeans rolled over pristine ankle height lace up boots. Dean knew he was reading Benny reliably, but it still thrilled him to speculate over his interest in Dean as a customer. Dean widened his stance and flexed his arms, testing the nearly flawless fit. He felt unstoppable.

“You know, I was toying with the idea of making a set of pants to match. Sound like something you’d be interested in?” Benny locked onto Dean’s grass green eyes in the mirror. “Give ya deal. Just need to get your particulars and I could have them for ya in a week or two.”

“Oh yeah?” Dean’s eyebrows hitched; he licked his lips challengingly at the large man standing behind him. “How much of a deal we talkin’ ‘bout?”

“Why don’t you step into the dressing room and we can see what we can work out?” Benny’s voice was maple syrup, dark and sticky on Dean’s ear. Dean’s body gave him away, the cold chill racked his torso as his blood traveled south. Dean didn’t say a word he simply straightened to his full height and ambled through the tavern style white door beside the mirror.

Benny clicked the lock behind them before plucking his measuring tape from his shoulders. Dean’s eyes were on their feet, waiting for Benny to make his move, unwilling to be the one to break first.

“Why don’t you step up there, doll? Just need to take down your measurements,” Benny led Dean to a raised platform in front of another set of mirrors. Dean’s eyes flashed in understanding, casually he adjusted himself as Benny dropped to a crouch, pencil in his teeth. He held the yellow plastic to Dean’s hip and followed the strand down to the cuff of Dean’s jeans.

Dean didn’t know where Benny had pulled the scrap of paper from, but he waited nervously as Benny wrote down his length. Benny’s heavy palm braced against Dean’s thigh as he settled onto his knees. Dean’s eyes shot to the ceiling as the tip of the tape was rutted into his inseam, his hand shooting forward to find Benny’s shoulder to cling to. But Benny’s touch disappeared all too soon, as he took down another number. Dean whimpered as Benny found the top of Dean’s fly before trailing down the zipper into the crux of his jeans and the reinforced seams that cradled his balls.

“Might not be too accurate, but I’ll keep it for now,” Benny murmured below Dean, Dean was barely holding back now. Before he could reply Dean felt thick fingers plucking open his belt buckle. “How ‘bout I go about my side of the deal tonight and then we can talk details later?”

Dean grunted and swallowed. “Yes, um-hm,” he gasped as Benny pried his jeans open.

Benny hummed in adoration, warm breath tickling the patch of hair along Dean’s front as he yanked both layers of fabric down Dean’s impressive thighs.

Somewhere in the world beyond them, an electronic crinkle sounded through the mall.

“Attention mall shoppers, the time is now nine pm and we are closed. Please make your final purchases and head to the nearest exit. We will reopen tomorrow morning at ten am. Thank you for your patronage and have a goodnight.” A steely feminine voice echoed into the night as the sound of a massive light switched off.

“I, uh, don’t want to keep you from closing up,” Dean whispered, thumb drawing tiny circles at Benny’s temple without looking down at him.

“’S alright. Trust me?” Benny took hold of Dean firmly. Dean hissed; lust blown eyes meeting questioning, glimmering blue. Dean nodded, brushing his fingers over Benny’s short hair, gently bringing Benny closer while pulling his shirts out of the way.

Benny stroked Dean’s length, eyes drinking in Dean’s reactions while feeling Dean harden further. Dean’s mind short-circuited with the hot wet pull from Benny’s mouth. He groaned as Benny’s tongue toyed the underside of Dean’s shaft, all the while taking him deeper still. Before he was prepared, Dean felt the satisfying burn from Benny’s facial hair as it rutted into his sensitive skin. Dean stumbled back, falling from Benny’s mouth as his back hit the mirror behind him.

Benny chuckled, crawling like a jungle cat towards Dean. Benny’s large hands squared Dean’s feet for him beneath pants-locked knees. “You alright up there?”

“Get over here,” Dean growled, leaning to pull Benny up by his armpits, but Benny slipped from Dean’s grasp, trailing teasing kisses over Dean’s bare thighs, before grabbing two fists full of Dean’s taut ass.

“’m fine where I am, darlin’,” Benny purred before whining around Dean’s cockhead once more.

“Uhhh, you’re more than—fine,” Dean praised, letting his head fall back against the cold mirror with a dull thud. Enjoying the feel of Benny’s face in the palms of his hands, heavy, real, urgent. Benny massaged Dean’s sack, middle finger snaking back to hit that spot that made Dean’s eyes slam shut. Dean felt like he was floating, mind blank as the pleasure pooled deep inside him, his shoulders shoved against the looking glass and feet on the floor the only points tethering him to this world. The delicious sight of Benny’s hollowed cheeks as handsome as they were strong, coaxing him closer to release.

Dean met Benny’s lips with shallow thrusts, pushing them both to their limits before freezing in place as he came, with a shrill moan, against the back of Benny’s throat. Benny swallowed dutifully, tongue pulling every ounce Dean pumped into him. He grinned mercilessly back up at Dean’s heaving form, eyebrows pitching suggestively as Dean caught his breath.

“Now get up here, will ya?” Dean demanded, half-heartedly yanking Benny by the collar of his shirt until he stood, diving headfirst into a bruising kiss. Dean moaned at the taste of himself on Benny’s tongue, thigh instinctively slipping between Benny’s, grinding into Benny’s clothed cock.

“I should be getting back to it. It’s late.” Benny sighed into Dean’s neck. Once Benny caught his lover’s disbelief in the mirror, he threaded his hands around Dean’s thinner waist, holding him at arms’ length until he caught those green eyes straight on again. “Hey, it was fun. If you want that jacket, we better get you rung up.”

Dean nodded, stealing a quick kiss to Benny’s throat before bending down for his pants. Not five minutes later and Dean was slipping his wallet into his back pocket. Jacket still on, tags and all.

“Sorry, didn’t catch your name, Cher,” Benny crooned, holding out the receipt for Dean to take.

“Name’s Dean. Thanks for such— attentive service, Benny.” Dean smirked, accepting the slip with a lingering drag over Benny’s thick fingers. Dean winked, letting his cockiness slip out again as he tucked the receipt into the inside pocket of his purchase, bottom lip dimpling under the pressure from his top teeth. Benny stopped himself from leaning across the desk and sucking that lip into his own mouth, but only barely.

“Pleasure’s all mine, Dean. Hope to see ya soon,” Benny walked Dean to the door, waiting to lock up.

Dean nodded, scratching the back of his head. “Definitely, when I get a chance I’ll be in touch about those pants. Have a good one, and thanks again.” Dean offered Benny his hand, firmly holding on while his left hand gave a gentle cup of Benny’s bicep.

With a parting glance Dean walked out of the store, sizzling with possibility. Benny watched him practically strut to the doors down the half-lit hallway, appreciating the view.


	2. An Open Tab

**Summary for the Chapter:**

> Written for: @spnkinkbingo and @thoughtslikeaminefield
> 
> Square Filled: Bear
> 
> Word Count: 1731
> 
> A/N: 18yo+, Benny’s turn to visit Dean at work this time. Internalized bi-phobia, objectification, sexual tension.

It was another Friday night at the bar, Dean was slinging drinks and Anna and Bella were waiting tables. Jack was decidedly late, again. Dean bobbed his head to the music and tried to stop watching the old smoke stained clock on the wall. It was the second week in a row and Dean was no longer interested in giving Jack the benefit of the doubt.

Dean had been helping Cas out at the bar for six months. Cas, one of Dean’s closest friends, talked Dean into bartending on an as needed basis, since the college kids Cas hired had been notoriously flaky. ‘As needed’ had somehow become Dean’s taxing second job. Which was how when Cas’s own nephew couldn’t bother to show up on time, Dean was left to step up, again.

The afterwork rush was heavier than normal and the music already seemed too loud. Dean just finished pouring the last of the beers for Anna to take back to the pool tables when Jack finally made his appearance, excuses flying out of his mouth. Dean knew he shouldn’t be so short with the kid, but Cas sure as hell wasn’t going to be.

“Save it and go help that group at the end of the bar, will ya? I’m already backed up.” Dean watched as Jack balled up his hoodie and shoved it beneath the register. The redheaded waitress gave Dean a knowing look as the hapless youth washed his hands.

It was going to be a long night.

Castiel Novak made his nightly appearance just after ten. Eight years ago, when he inherited the bar from his brother, Cas decided he needed to look like a business owner, despite his young age, so he started wearing suits. If the weather was cold enough, he’d even wear a trench coat over them. Dean never had the heart to tell Cas he was overdoing it and, of course, Cas never learned better on his own.

There was a time when Cas’s obliviousness had been endearing to Dean, but lately it only seemed to add to Dean’s exhaustion. Dean guessed that showed progress. Then again, he was still the dancing monkey behind the bar because Cas needed him there, so maybe it wasn’t a lot of progress.

After so long, Dean had learned to pick Cas’s voice out of the crowd, from any point in the room; unintentionally clocking his path like a sonar. Dean finally put eyes on Cas when he made his way to check in with a few of the regulars at one of the booths. He saw Cas again when he initiated some awkward small talk with the waitresses. Lucky for them, they were too busy to be stuck on Cas duty for long. By the time Cas got behind the bar, Dean had a pack of women in one corner that refused to let him walk away. Which left Cas to figure out the shape of things all on his own.

Jack could barely answer Cas’s questions; he was so overwhelmed with orders. After turning down a second round of shots with the ladies, Dean lost track of Cas. After ten minutes, Dean figured Cas had left for the night, easing any anxiety Dean had held for the remainder of his shift. If Cas was gone, Dean didn’t have to play too nice with the kid and he could close without too much hassle.

Which was exactly when Benny walked in the door.

Dean didn’t realize Benny knew where he worked, but Benny sure as hell meant to find him there. It had been two weeks of dirty texts since they met, and Dean nearly jumped over the bar to kiss him; he was so excited. But then Dean remembered where he was and what he was: in his longtime crush’s bar and still in the closet.

He doubted it would hurt his tips at this point in the night, but a fat dose of reality was the next best thing to a cold shower he could get.

Dean nodded at Benny, tongue teasing the back of his teeth. “How’d you find me?”

“A girl’s got to have her secrets,” Benny chided. “I’ll take a bourbon, if you’d be so kind.”

Benny reached into his back pocket and Dean tisked at him. “C’mon man, your money’s no good here.”

“Is that so?” Benny smirked, before taking a lip smacking sip of the double Dean had poured him. Dean couldn’t wait to feel that stubble burning his skin once more. “What if I want to show my appreciation for the fine service?”

Dean shook his head and licked his lips. “What?” Benny blanched.

Dean leaned in and whispered a reasonable six inches from Benny’s ear. “After the fine service you gave me, you’ve got an unending tab,” Dean insisted.

Benny chuckled, rich and melodic. It made Dean feel like a teenager, so eager to hear that laugh again. A couple sat down beside Benny and Dean got pulled away into a string of orders after that. Jack, apparently, had given himself a break, and left Dean to hustle for a solid thirty minutes alone. All the while, Dean made sure Benny’s drink was filled.

Once Jack returned, Dean bailed. “Hey, I gotta grab some stock, your turn to do the one man show.”

Without a passing glance to Jack’s stunned face, Dean rounded the bar and nodded Benny to follow. Dean headed straight down the back hall, which led to the coolers and the office. Benny was a casual ten paces back. The second the walk-in’s door closed, Dean pushed Benny against it. Dean’s lips desperately latched on to Benny’s mouth. A mouth and beard that felt even better than Dean remembered.

Benny took Dean’s face in his massive hands, and slowed the kiss, drawing it out, and savoring it. He leisurely turned them until Dean’s back was the one pressed to the door. Which made Dean sigh just as Benny broke the kiss. Dean hooked his fingers into Benny’s belt and dragged him closer.

“You drive me crazy, you know that?” Dean snipped, slotting his thigh between Benny’s.

“I had a notion.” Benny half smiled. “How long we got back here?”

“As long as we need. Forget the kid, he can figure it out.” Dean moaned as Benny lifted him off his feet with the nudge of his thick thigh between Dean’s legs.

“You say that like you actually are gonna leave him hanging. We both know you’re not that guy,” Benny teased, breath ghosting over Dean’s throat.

Dean blushed. “Yeah, you’re right, but I don’t want to think about leaving yet,” Dean whispered, hands sliding under Benny’s shirts and roaming his barrel chest. Dean could only imagine the power behind all that breadth. Benny sucked on Dean’s pulse point and began to rock into him.

Dean slid his fingers through Benny’s chest hair, relishing in the manly down. Dean dropped his left hand to palm Benny’s covered cock. The weight of him in Dean’s hand only fueled them both. Benny took Dean’s gasping mouth once more and they fell to a place beyond words.

The bass of the music pounded through the insulated walls, the only reminder of where they were at all. Dean started to undo Benny’s fly when suddenly the melody line and a cacophony of voices flooded the cool air. Dean hadn’t realized they had moved off the door until it was already open.

“Hey! There you are! Jack said you were getting stock. We’re out of Light and—,” Cas trailed off. “Is everything alright?” Cas eyed Benny suspiciously.

Dean cleared his throat and shrugged, arms swinging awkwardly. “What? Yeah, everythings fine. Just grabbed an extra pair of hands for the kegs, man. Why?”

“You seemed flushed, Dean,” Cas noticed. Of course, Cas had suddenly become observant at that moment.

“That was Light and Hacker-pschorr, boss?” Benny interrupted.

“Yup. Alright, Cas, thanks. Why don’t you go and tell Jack we’re on our way?” Dean patted the door frame to get his point across. The door swung closed as Cas, still squinting, turned to go.

Dean unapologetically adjusted himself in his jeans as Benny dragged his fingers over the labels on the rows of silver barrels.

“Sorry about that,” Dean whispered, not looking Benny in the eye.

“Hey,” Benny called out to him, reaching for his elbow. “No matter to me who sees us. You good, cher?”

Dean inhaled deeply through his nose, and nodded. “Yeah. Or, I will be.”

Benny cocked his head and gave Dean an understanding smile. “It’s like that, huh?” Benny guessed.

Dean closed his eyes at the disappointment he was sure to see etched onto Benny’s face. “I didn’t— Sorry, this isn’t fair to you,” Dean tried.

“Oh, Dean, that’s your battle to fight. But just so you know, I don’t scare so easy,” Benny winked at Dean and squatted down to lift his keg.

Dean about melted on the spot. How’d somebody like him find such a class act? Benny shuffled out of the cooler.

With his eyes on Dean the whole while, full of silent promises, Benny backed out of the door. Dean pinched his forehead and sighed before bending down to grab his share of the load.

“Coming through!” somebody bellowed.

Back to reality they went, with a whistle and a string of cat calls announcing their passage through the packed bar. Dean could have sworn he heard just as many appreciative male voices as female ones and he tensed in fear. He didn’t usually feel so exposed, but Cas’s interruption was just another reminder of all of the parts of himself he was used to being hidden.

“That’s my kind of bear, alright,” a skinny guy gushed to a petite brunette. Dean rolled his eyes, but he couldn’t blame the man for ogling Benny. He certainly was all bear.

Once Dean was back behind the bar, he felt suffocated with the amount of people surrounding him. He managed to hook up the kegs quickly, leaving Cas and Jack both breathing sighs of relief. Dean looked passed them to find Benny, who tipped his head and gave Dean a wistful salute.

“Thanks, Benny. I’ll be in touch,” Dean called out over the ruckus of the crowd, hand raised in a motionless wave.

Benny lifted his chin in agreement and disappeared out the side door.


	3. Qualit Assurance

**Summary for the Chapter:**

> Dean’s pants arrive. How should he best thank Benny for his hard work? Text messages are in bold.
> 
> Warnings: Flirty boys, dick pics, cum shots, masturbation, dirty talk. Dean finally gets to see what Benny is packing.

The familiar grumble of the impala’s engine was Dean’s soundtrack to his drive home that following Tuesday. For one, he was too distracted to turn on the radio on the short ride home. And secondly, Dean was wiped from another ten hour day at the garage followed up by overthinking about if and when he’d get to see Benny again. He was half hoping and half terrified he’d lost his chance after Cas interrupted them in the beer cooler.

But Benny said he didn’t scare easy, Dean told himself like a mantra.

Dean arrived home just after six to a neatly wrapped brown paper package on his doorstep. The ink stamped return address in the corner was all the confirmation Dean needed and he couldn’t help but swallow at the sudden reality in his hands. His pants were done. Benny had mailed them out from the shop because Dean was always too fucking busy to get back to the mall and claim them.

Benny was leaving it up to Dean now.

He marched up the porch and let himself in, hanging his keys on the hook by the door. He set the box on the landing before he shrugged out of his jacket, fresh leather smell still prevalent. The scent immediately took him back to the changing room when Benny measured and pleasured him. Dean’s skin prickled at the mere memory.

But now he had to deal with the consequences of that night. What was Dean supposed to do with a pair of leather pants? He couldn’t just wear them out. Could he?

He ran his knuckles over his jaw and turned toward the kitchen. Dean needed to think and he couldn’t do that properly on an empty stomach.  
image

Two hours later Dean had run out of things he could do to avoid opening the package from Benny. He had cooked himself a full meal of steak and potatoes; he even muscled down some green beans soaked in butter. Then he cleaned up after it all. He started a load of towels and checked the local news. Dean opened his second beer and sauntered over to the steps. 

He knew he wouldn’t be able to sleep if he tried leaving it until the morning, so he bit the bullet and took the box up to his room. The brown paper revealed a sturdy white cardboard also stamped with the shop’s logo in the bottom right corner, classic and clean. Dean pulled the wings from the front and found his pants nestled in a thinner brown paper wrapping secured with twine. In the knot there was a simple note on a square of canvas, below the general business gratitudes Benny handwrote:

I can’t wait to see how they fit. x B

Dean thumbed Benny’s careful handwriting as he untied the bow. He couldn’t help but bite his bottom lip with a sudden bashfulness. The pants were flawless; color the same rich, chocolate brown of his jacket with pockets that matched on the seat. They weren’t flashy, but enough of a detail to make a matching set. The leather was heavy yet pliant in his hands.

He shook them out and held them to his waist, they seemed to fit. As he set them down on his bed, he was hit with a sudden wave of inspiration. He pulled his phone out of his pocket and opened his messages from Benny while he polished off his beer.

**Dean: Got your package. They’re awesome. **

**Benny: Yeah? That was fast. How they feel?**

**Dean: I was just about to try them on.**

**Benny: By all means**

Dean felt compelled to put on a show, so he dropped to his bed and unlaced his boots then took off his socks. He stood and dropped his jeans, palming his growing excitement before he picked up his phone again. Then, with that same swagger he managed the first time they met, posed in front of the bathroom mirror in his boxer briefs.

Dean sent the selfie with a simple winking emoji. Before he let himself get distracted by Benny’s reply Dean sauntered back to his room for the leather pants. He pulled them up, hopping onto the balls of his feet. Though they were tight, they slid up his thighs and hugged him in all the right places. He went back to stand in front of the mirror and spotted the outline of his underwear beneath the fitted hide. His phone chimed with incoming messages. He sighed deeply and dropped the pants, stepping out of them and the cotton of his shorts in one quick two step.

Dean stroked himself and eyed the pants suspiciously. Benny definitely knew he’d have to go commando to pull those off. Dean’s ass tensed as he tugged harder, imagining Benny behind him before he stepped back into the leather. He tucked his erection against his leg to safely zip the fly. Then Dean took in his appearance once more; the pockets draped over the curves of his ass while the front barely contained his bulge, his nuts and cock on full display.

He almost whined at how hot he felt in them and at the disappointment of having no place to show them off. He teased himself through the stiff leather and took another picture to send to Benny. And another from the side. And one behind his back. Dean blushed and licked his lips as he typed, the heat of anticipation making his blood sing.

Once he had finished attaching the pictures, he scrolled up to see what Benny had sent when he was changing.

**Benny: Tease**

**Benny: So fucking pretty tho**

The text screen told him Benny was typing and Dean cupped his balls through the leather and thumbed against his dick as he waited, keyed up and needy for approval.

**Benny: Fuck me. Thats some fine craftsmanship… if I do say so myself **

Dean bit back a grin and responded lightning quick, tongue sticking out in mischief.

**Dean: I’ll be sure to pass on the message to the folks.**

**Benny: Somebody thinks hes funny. Its a good thing ur cute **

**Dean: I thought I got by on my charm **

**Benny: Dont flatter yourself Cher Those pretty eyes alone have got u places n u know it **

Dean had undone the zipper to stroke himself lazily, leaning back against the sink. He wanted to keep Benny purring; he needed to see him too.

**Dean: What have you got on big guy? **

**Benny: Oh now you’re curious**

Dean didn’t bother to respond with words, he just snapped a picture of his dick in his tight grip and sent it to Benny. 

**Benny: No cumming on my pants boy**

Dean chuckled, but stroked himself harder. After Benny didn’t reply or answer his question, Dean tapped his name on the screen, which brought up the call option.

“You know how fucking hard it is to put these on knowing you sewed every stitch thinking about me? My body? My dick?” Dean was beyond pleasantries. “And I’ve never seen you? That fat fucking cock that I only got a quick hand on?”

“You’ve got a dirty, whore mouth, you know that?” Benny hissed over the line. “I’m at the store, Dean. Give me a minute to get some privacy, Christ.”

Dean’s stomach fell, of course Benny had to work late. Only he was still rewarded with a picture in return: Benny’s meaty hand groping over his white briefs. Dean groaned, mouth watering, he spit in his palm and started stroking himself with abandon.

“Oh fuck! Where are you? Can you touch yourself?” Dean asked with his eyes slammed shut, bottom lip firmly bitten once the words were free.

“Now, see, being the boss has its perks. Got me a lock on the office and everything,” Benny drawled. “You should see it sometime.”

“Uh-huh,” Dean swallowed. “You just name the time and I’ll be there.”

“Dean, slow down now, lemme catch up,” Benny reprimanded in his slow sinful accent.

Dean grunted onto the line, about to throw the phone and come without him. But he did interrupt Benny at work, the least he could do was play along. Dean squeezed his head and exhaled slowly. “Yeah, uh, okay,” Dean panted.

“That’s it, doll,” Benny praised. “Been riled up since the bar, shame we couldn’t hash it out right then and there.”

Dean smiled and flicked his dick, holding himself back as Benny’s voice grew more hoarse. “Nah, I need more time with you than that,” Dean contradicted.

“There is something,” Benny groaned. “To say for waiting.”

“Not much longer though. Fuck, I want to taste you.” Dean grabbed his dick again; the phone was pinned to his ear by his right shoulder so he could cup his balls.

“There’s that dirty mouth again, such a naughty thing with such a pretty package,” Benny crooned. 

“You can shut me up whenever you’d like,” Dean promised.

“Oh, I can and I will,” Benny agreed and then his voice dropped lower. “You close? I wanna hear ya.”

Dean whimpered, thighs clenching as he started to frantically build to his orgasm. He thought about Benny’s thick fingers spreading him open, pushing him down and fucking him hard. He gasped and unleashed. Benny’s name gained four syllables as he came.

“Yessir, that’s what I like to hear,” Benny’s voice grumbled like oncoming thunder. “Dean, baby, I can’t wait. I’m—”

Benny broke off into a string of muttered expletives, Dean shuddered on his end of the call as he pumped his deflating cock. “God I can’t wait to take that,” Dean murmured, all blissed out and sweet on the man that had blindsided him.

Benny hummed in acquiescence. “‘fore you clean up, show me your mess.”

“I didn’t get it on the damn pants,” Dean sassed, exasperated.

“Fair enough, but I’m sending you mine all the while,” Benny replied. Dean groaned and pulled the text conversation back up on the screen. He double checked that the leather around his thighs was unblemished before taking a picture of his sticky fist with the bathroom mat in the background.

“Happy?” Dean goaded, as he turned on the sink to wash up.

Benny whistled in appreciation. “Yeah, you?”

Dean hadn’t noticed Benny’s picture come through; he scrambled for a towel to dry his hands before swiping back to the exchange. There against a dark wooden desk was a spattering of jizz just below a thick, hooded dick, which was nearly twice as long as Benny’s palm was wide. Dean swallowed so hard he started to cough.

“I’ll take that as a yes, sugar?” Benny teased.

“God, yes,” Dean stammered as soon as he could clear his throat.

“I better get back out there, Dean.”

“Yeah, I gotta wash up before bed,” Dean agreed. “Talk soon.”

“Sweet dreams,” Benny puckered his lips and ended the call.

Dean dropped to his elbows over the sink and splashed the still running water over his face and neck. When he felt like he could stand steadily again, he stripped off his shirts and his pants, careful to avoid stepping in his cum on the rug. He bunched up the assorted soiled bits and tossed his pants on the bed as he headed back down to switch the laundry. It had been awhile since he paraded around his own place naked and he felt oddly justified in doing so.

Once the wash cycle was set, Dean grabbed another beer and headed back to his room. He folded the leather pants back the way they came and stored them in the box on the floor of his closet for someday. He threw on a pair of pajama bottoms and double checked his alarm.

Finally, Dean settled into bed and got comfortable. He scrolled absentmindedly through social media as he sipped. Just as Dean finished his beer he got a text from Cas asking him to start at 6 instead of 8 on Friday. Dean’s thumb hovered over the message, but Dean broke from habit and left Cas on read for the night. Then he rolled over and fell fast asleep.


	4. Wine and Dine

**Summary for the Chapter:**

> 18yo+, Super long chapter for this series, bear with me! We get some Winchester backstory, fear of commitment, Benny being a dream, fellatio, Dean being needy, anal fingering, unprotected anal sex (be smart about your own sex lives, this is fiction), dirty sweet talk, hand job, and fear of discovery.

Dean’s head and shoulders were hidden in the underbelly of a worse for wear minivan when Sam arrived at the shop. It was a Thursday and Sam’d finally gotten together the paperwork John had insisted they sign before his next back surgery. He just needed Dean’s information and signature to get his dad off his ass. The smell of oil hit him as he walked in the wide door. It was as familiar as the harsh sounds of machinery and the classic rock that filled the four stall garage.

“Sam?” Bobby asked in surprise. The older man’s face fell in annoyance. “Don’t tell me that hybrid is already giving you trouble.”

Sam laughed. “Car’s running fine, Bobby. I’m just here for some legal stuff for the folks.” He lifted up the folder to show their surrogate uncle and shop owner the business at hand.

“Give him a minute, he’s almost finished with that axle,” Bobby wiped his hands on a spare towel. “Coffee? Ellen’ll love to see ya.”

Sam considered. “Why not?”

Bobby screamed over the noise, alerting all of his mechanics, “I’m heading inside a minute.”

Rufus, Lee and Gordon all showed Bobby they had heard. “Dean! Sam’s here when you’re done with that mess.”

“Sammy!” Dean called out in greeting. “Be there in a few.”

Ellen’s wide smile and smokey voice welcomed Sam into the waiting room, she disappeared behind the counter and came out the side door. She marched up and gave Sam a big hug, her small frame nearly lifting his towering body off the floor.

“Geez, boy, you’d think you still lived in California with how often I get to see you. How’ve you been?” Ellen insisted.

“Sorry about that.” Sam gave Bobby a look and Bobby shook his head in a “don’t drag me into this” sort of way. Ellen pulled back and took stock of Sam.

“Well, at least I know you’re alive between bowling and what I can get out of Dean. How’s your daddy?” Ellen stood with her hand on her hip.

“Still as pissy as ever, getting himself worked up about dying. Which means he’s taking it out on Mom, Dean and me. I need Dean’s signature on power of attorney forms,” Sam explained.

“Power of attorney? Aren’t you a lawyer? What’s he need it in writing for?” Ellen looked to Bobby to explain John’s logic.

“Beats me, but it’s probably ‘cause he only trusts Dean to do what he asks,” Sam answered.

“What an idjit,” Bobby muttered.

The chime sounded at the front door, alerting Ellen to a new customer. She spun to greet them. “Well, tell your mama I said hi. And tell your daddy to get the stick out of his ass,” Ellen told Sam in a rush.

She went back through the door that led to their simple office before appearing behind the counter once more. They shuffled awkwardly to the small seating area. Bobby grabbed a styrofoam cup off the stack and filled it with coffee, handing it to Sam before making one of his own.

“How’s that little brunette treatin’ you?” Bobby asked, knowingly.

“Ruby’s fine. I just work too much, I guess,” Sam shrugged, staring into his coffee as if it would change the conversation for him.

Bobby hummed. “We’ve all been there.”

Dean arrived just in time to save the men from any more forced conversation. He was dirty, his coveralls peeled down and bunched around his waist.

“Everything okay?” Dean asked, concern laced over his features.

“Yeah, man, calm down.” Sam smiled. “Dad’s just being paranoid, wants you to sign a few things.”

“You need them now?” Dean asked, checking each palm and wiping them on the seat of his pants.

“Yeah, I told Dad I’d get them last night, but left them at the office before I made my way to the alley,” Sam said. “Sorry.”

“No biggie.” Dean shrugged. “Want to grab lunch? I should clean up a little before I sign your official documents.”

“If Bobby’s cool with it.” Sam and Dean both looked to Bobby, eyes begging like they were kids after sweets.

Bobby rolled his eyes. “Oh, Christ. You bring back something for everyone, you hear?”

Dean cackled in triumph as Sam took the cash out of Bobby’s outstretched hand.

“Thanks, Bobby!” They called in unison as they headed out the door.

In the parking lot, Sam leaned against his own car as he waited for Dean to get the orders from the other guys and Ellen. Dean came strolling out ten minutes later, cleaned up with mischief brewing behind his eyes. This was as close to playing hooky as he could get.

“When’d you get that?!” Sam asked in shock, an impressed look on his face.

“You like it? Custom-made,” Dean popped the collar of his leather jacket. “Got it off a guy at the mall, actually.”

“I guess all those tips you get from helping Cas are paying off,” Sam replied, sinking into the passenger seat of the impala.

“Something like that,” Dean answered, pulling the driver side door shut.

^*^*^*^*

Benny lived outside of town on the edge between farmland and forest. The house was a washed out yellow that glowed from the inside out, like a beacon in the fading autumn light. He had a half of a rundown barn on one side of the property and a fresh one and a half car garage on the other.

Dean sat in the driveway, worrying himself sick.

He started to wonder if this was what he wanted and it scared the shit out of him. He’d never gotten this far with a guy before. Sexually, he had gone farther. But he’d never had a planned date that was anything more than a roll in the sheets. But Benny insisted, they’d talk and eat, get to know one another. And Dean wasn’t sure if he should bring flowers or extra lube. He’d settled on bourbon and prayed his manners wouldn’t betray his nervousness.

He clutched the brown paper bag around the neck of the bottle and crawled out of the driver’s seat. He over thought as the gravel crunched beneath his boots. Dean had left the leather pants at home, having come straight from work after Bobby made him stay late to make up for his extended lunch break with Sam. He didn’t think he would have worn them anyway, but the reasoning made him feel a bit better about showing up in his usual jeans. After a quick deep breath and shaking out of his shoulders, Dean knocked on the screen door and called inside, “hello?”

“Door’s open!” Benny replied from somewhere in the back of the house.

“Right,” Dean said to himself.

He found himself in a small living space, which was cast in shadow from the brilliant lights of the kitchen. Benny had a towel over one shoulder and a charming grin across his face. Dean strode over the hardwood floor, passing a hallway on the left. Benny met him at the half wall that broke up the kitchen from the living room. Beyond the kitchen was a small dining space surrounded by windows, it must have been a porch at one point.

“Glad you could make it,” Benny’s eyes twinkled as he leaned over the counter and pecked Dean square on the lips. Which stunned Dean into a slight fog, when he collected himself, he handed Benny the bottle.

“Sorry, if I’m late, work got away from me,” Dean apologized, scratching the back of his neck.

“It’s 7:05, Dean. I’ve waited nearly a month to get you to myself, I think I can handle five minutes,” Benny assured. Benny appraised the alcohol. “Shall we?”

Benny talked as he cooked, leaving Dean to rest back against the island and sip his whiskey. Most importantly, it gave him the chance to Benny-watch. His host wore brown Dickies and a white henley shirt, which accented the broad curves of his shoulders. Benny drawled on about how he ended up in Kansas (an ex from Nebraska), and how he’d started in the trade, which went back three generations.

For a hometown boy who’d barely left Lawrence, Dean felt dull in comparison. But Benny didn’t look at him like he was boring.

Dean started talking once they sat down to eat. Little things at first, like how he and Sam had the highest averages on their bowling team and about how Sam was always the brother with the book smarts, while he was just another gear head like his old man.

He laughed through explaining how Mary always had them over for Sunday dinners, but still relied on take out instead of cooking it herself. It was surreal, in a way, he hadn’t had anyone he needed to explain so much about his friends or family before. Everyone seemed to know everyone already, even though it wasn’t a small town. If Dean had been introduced to someone, they already knew him by reputation, or as Mary’s oldest or as Sam’s big brother, or just as one of the boys at Singer’s.

It felt nice to tell his own story. It felt even better having Benny listen.

Benny stood to clear their plates, the food had vanished between their rolling conversation. Dean mirrored him, reaching out to stop Benny from grabbing his plate too. “Let me clean up? Least I can do.”

“You wash, I’ll dry?” Benny countered, snaking his free arm around Dean’s waist to give him a squeeze.

Dean beamed at him. “Deal.”

They kissed, in a syrupy sweet, no rush at all kind of way.

Dean stepped closer, points all along his body searching for Benny’s. He drowned in the sensation, letting his mouth give and tongue take in a way that had never mattered before Benny. It was different than their past kisses, smoother somehow. This one felt like it meant something. Dean froze at the thought and slowly broke away.

Dean cleared his throat.

Benny opened his eyes slowly, teeth glinting as he dragged his tongue over them. “Spoil sport.”

“They’re your dishes! My mom would have my hide if she heard that I left the clean up for someone who cooked for me.” Dean shrugged.

“The same mama that don’t cook much, huh?” Benny considered.

“Yeah, well, you don’t question Mary Winchester.” Dean sighed out a chuckle and side stepped Benny, his whole place setting piled into his hand.

“I’ll keep that in mind,” Benny murmured, following Dean to the sink.

When the dishes were nearly done, Benny leaned over and dropped a scratchy peck on the back of Dean’s neck. Dean shivered, but kept scrubbing. Benny’s mouth trailed above Dean’s collar with building insistence, the warmth spread out from each tiny connection. When he reached Dean’s jaw, he nipped just hard enough for Dean to sigh in resignation. Dean shifted on his feet, lowered his shoulders and dropped his head, giving in to Benny’s affections.

Benny braced himself on Dean’s waist, tongue soothing over each bite he left. He rubbed his bearded cheek along Dean’s stubble and hummed in satisfaction.

“You ready to head upstairs, cher?” Benny purred, his seductive drawl made Dean twitch in his pants.

Dean turned to look Benny in the eye, and lost every thought in his head by falling head first into those sparkling blue pools. And Benny said Dean had pretty eyes.

Instead of answering, Dean tilted his chin and took Benny’s mouth with his. This kiss had the fire from the bar and the mischief from the changing room, it was everything they had shared and all Dean hoped to. It was the only reply Benny needed. Benny leaned into Dean with his whole body, pushing Dean’s ass against the sink.

Dean grunted from the pressure, before grabbing Benny’s face and letting their tongues dance. He could feel Benny’s dick through the thick fabric of his pants, straining and urgent. He rocked his hips into it as his own erection swelled.

“Are we even gonna make it up stairs?” Dean teased, and began unbuttoning Benny’s shirt.

“Don’t bother me none. We got all night,” Benny agreed, pushing Dean’s flannel off his shoulders. They kissed and undressed each other, like it was a game of tag. Dean stopped Benny when he reached for Dean’s belt.

“Nu-uh. Gimme this,” Dean hissed, making a point of sliding onto his knees, trailing kisses over Benny’s barrel chest on the way, to open Benny’s fly instead. Dean rucked Benny’s pants down to his thighs. Dean sucked on his stomach, just above the waistband of his briefs. Benny brushed his fingers over Dean’s hair, resting his elbow on the counter top and watching Dean with amusement.

“Go on,” Benny prodded when Dean paused under his touch.

“Yeah, yeah, I’m getting to it,” Dean huffed, dragging Benny’s final layer out of his way. “Fuck, look at you.”

Benny’s eyebrows raised in mild surprise, he wasn’t used to getting such flattery. Though Dean hadn’t seemed to hold back much. Dean’s eyes were transfixed on Benny’s cock, watching it gently throb now that it had been freed. The thick base and soft sheath of flesh protecting his crown were a new puzzle for Dean to solve.

Dean took it in his right hand and began to stroke him experimentally, leaving sloppy kisses across Benny’s hips as Dean gained a rhythm. Dean licked his lips and went for it, sucking Benny’s hooded cock into his mouth. He drew back and lapped at Benny’s foreskin before teasing the tip with kitten licks. Benny inhaled sharply and Dean felt encouraged enough to continue. He pumped Benny at his base, switching hands to cup his balls and tease his taint.

When Benny’s hands clamped around Dean’s temples, he knew he had been taunting him long enough. With practiced control, Dean took as much of Benny’s thickness as he could. The extra skin added to the pressure in his throat as he swallowed consistently around him, hollowing out his cheeks. He prayed he wouldn’t lose his dinner, he was so full. Dean was choking on Benny’s cock by the time Benny pulled him up for air.

“You goin’ for broke?” Benny panted, dragging Dean up his body for a kiss.

Dean pulled away to check, “was that– was I– I wasn’t sure if?” He smiled shyly.

Benny’s face softened. “It was phenomenal, sugar. Top notch cock sucking.”

Dean sighed in relief and Benny kissed the next breath out of him, rutting his spit soaked dick against the smooth plane of Dean’s tummy. Benny reached down and squeezed Dean’s ass with his whole hand, right in the crease. Dean unconsciously popped his ass out, asking for more. Benny grunted into Dean’s mouth and dug in with the tips of his fingers, bunching Dean’s shorts and jeans tight against his hole.

“I want you in my bed, doll. Get this tight ass up stairs before I bend you over the counter,” Benny warned. Dean swallowed back a whine and sucked Benny’s bottom lip into his mouth.

“I’ll take it however you wanna give it to me,” Dean replied, voice deep with the confidence Benny was used to.

“Yeah, I bet you would. That’s why I’m tellin’ ya to get up stairs.” Benny pushed Dean upright. “Needy little thing, trying my best judgement.”

Benny pulled up his pants to make it to his bedroom unencumbered. Dean followed behind, adjusting himself through his jeans. At the end of the hall was a small stairway that led to a wide open space, which Dean realized had once been the attic of the small farmhouse. It was finished dark wood with a matching bedroom set, pristine white sheets catching the glow of the moonlight through the triangular windows.

Dean would have put money on that Benny had done all the work on the house himself.

“Wow, this is some place you got, man,” Dean complimented, walking around the large bed to look out onto the fields.

“Thanks, it’s been a long time comin’,” Benny agreed, proving Dean right. Benny plopped down onto the bed and started taking off his shoes. Dean did the same on the far side of the bed. He stood and unhooked his belt, letting his jeans fall over his socks and boots. It’d been awhile since he’d been naked with another person and Dean tried not to over think it as he bent out of his boxer briefs. It was somehow more intimidating doing this with someone with the same hardware.

“Come on back here, now. No need to be shy, let me see ya,” Benny cooed.

Dean turned and faced Benny, in all his glory, across the bed. Dean’s breath caught in his throat, Benny was a huge slab of masculine strength, not exactly chiseled, but undeniably solid. Benny stroked himself lazily as Dean took him in. But Benny’s gaze was just as intently devouring Dean’s form, chin jutting out with hunger. Dean dropped to his hands and crawled towards Benny. Just before he reached Benny, Dean straightened and took his mouth in a fevered kiss.

On the bed, the height difference increased, leaving Dean, even on his knees, above Benny standing. Dean’s cock rocked into Benny’s belly, as Benny’s slotted against Dean’s thigh. They grinded against one another, letting the tension build as their hands explored the other’s exposed flesh.

Benny paused the kiss to slip his fingers past Dean’s swollen lips. Dean sucked them sloppy, twitching at the thought of how they’d be used next. Dean’s fingers dug into Benny’s back once Benny started to work him open, one meaty finger at a time. Dean gasped, bucking into the painful pleasure.

“God, you’re so pretty, Dean,” Benny whispered. Dean’s chest ached hearing his name instead of another of Benny’s passing terms of endearment. “You gonna come for me like this?” Benny took hold of Dean’s dick with his free hand. “Or do you need my dick too?”

Dean fought to keep his eyes open, the thick stretch of Benny’s fingers fucking into him matched in time with the coarse strokes of Benny’s palm, pulled him apart. He moaned, trying to remember his words.

“I’m still gonna fuck this pretty little ass, anyhow. Just figured I’d let you come first,” Benny promised.

Dean shuttered out a breath, and let his head fall to Benny’s shoulder. “So close, fuck, you– so good,” Dean sputtered.

Benny added a third finger and Dean’s vision went white, his balls hitched and for a few glorious seconds he was weightless. Then the violent jolts of pleasure surged through his entire being, spilling out over Benny’s fist and onto his chest.

“That’s it, hmmmm,” Benny praised. “Coming like a dream, so fucking hot, Dean.”

Dean couldn’t open his eyes; he felt the sweat cool on his skin as he was racked with aftershocks. The cold sent added shivers over his body and he fell to the side, limp, as Benny carefully pulled his hand out of Dean’s ass. Benny wiped his hands and chest off with a piece of his discarded clothing and smiled down at Dean.

Benny kissed the ball of Dean’s shoulder, and brushed the hair off of his forehead tenderly. Dean reached up and gripped Benny’s hand, kissing his knuckles before holding it to his chest as he caught his breath. Benny crawled on to the bed and slid behind Dean, careful to not let go.

Benny was an anchoring big spoon, with a single thigh wedged between Dean’s as he came down. Benny hummed an unintelligible melody while dragging his whiskers over Dean’s shoulders. Dean shifted, letting Benny’s cock notch along his balls, he was still so hard it sent another rush of pleasure through Dean’s body.

“That tickles,” Dean half heartedly complained, scrunching his neck.

“What, this?” Benny nuzzled in deeper, getting to the sensitive skin of Dean’s neck, until he was breathing thick and promising over Dean’s ear. “Can’t have you falling asleep on me.”

“Oh fuck no, nu-uh, I’m not even tired,” Dean asserted, turning to nip at Benny’s jaw. Benny chuckled, deep in his chest, shaking them both.

“So eager to please,” Benny growled, rolling his hips against Dean’s ass.

“Hey, it’s the least I can do, after all that,” Dean said, more seriously.

“You don’t owe me anything, darlin’. I’m doing this cuz I want to,” Benny assured. “Alright?”

“Me too. I haven’t wanted anyone so bad in so long– I guess I just want to make sure you stay interested,” Dean admitted, vulnerability closing his eyes and heating his face. Benny sucked on Dean’s pulse point.

“Well, I don’t reckon I’d ever not be interested,” Benny whispered, just as nervously.

To prove it, Benny rolled Dean on to his belly and rutted his dripping cock between Dean’s ass cheeks. Benny lurched off the bed and dug around his bedside table for his lube. As Dean pulled himself up to all fours, Benny carefully coated his cock before climbing back onto the bed. He dragged his dry hand down Dean’s spine, getting him to arch up so Benny could lube him open once more.

Dean groaned as Benny’s fingers slid inside him, still overly sensitive from his orgasm. Benny leaned down and sucked hard on the top of Dean’s ass, before centering himself behind Dean’s trim hips.

“You ready?” Benny checked in, gripping one of Dean’s cheeks as he rested his tip on the edge of entry.

“Hell yeah!” Dean shimmied his hips, searching Benny out. He dropped his head and waited for the pressure of fulfilment. His dick twitched, blood pooling to bring it back to life. Dean almost didn’t believe it himself, he was no longer that young.

Benny nudged inside, filling Dean up, inch by inch. Matching groans filled the wide room, deepening their connection. Once Dean took every inch Benny could give, Benny paused, reveling in the tight heat of Dean’s body, the pillows of his ass, and the muscles that flexed across his back.

“Now that is a sight,” Benny gushed, holding Dean’s hips fast in his strong hands.

Dean sighed and fell onto his elbows, fucking himself on Benny’s dick since Benny had refused to move. When Dean started to stutter, Benny took over with a satisfied hum.

“I think you need to let me do the work, cher,” Benny crooned. Then pulled completely out to slam back in. Dean cried out, head thrown back in anguished pleasure as Benny set his pace. It was deep and it was forceful, but he never rushed. Dean’s cock throbbed, drooling against the comforter. He was so thoroughly fucked that his vision started to cloud when a second orgasm roared up from the depths of his body.

“Ben– fucking– Benny, Jesus!” Dean called, spasming as he pumped himself through the onslaught.

Benny growled behind Dean, and increased his speed, holding Dean’s bottom half upright with authority. He landed a firm palm on Dean’s backside, clung to him, and came.

“That’s something wonderful right there,” Benny praised once he caught his breath, still rutting into Dean’s body, filling it with everything he had.

Dean felt the satisfying stickiness as Benny pulled out, the delicious filthiness that he had gone so long without. Dean slumped forward, face nestling on a pillow as his body headed toward exhaustion.

“You good?” Benny asked, dragging his fingers up Dean’s back as he stood.

“‘M so good,” Dean nodded, eyes at half mast, but he still managed to get a smug smile to peek through.

“Alright, sugar, I’ma go clean up. You need anything?” Benny offered.

“Just give me five minutes, I’ll be good to go,” Dean muttered, half in the pillow.

Dean didn’t last the five minutes before falling asleep. Fresh out of the shower, Benny found Dean half under the covers and snoring gently. Benny guessed Dean needed to be up around six, so he set an alarm and crawled into bed beside him.

^*^*^*

Dean awoke in silence, the quiet of the country was alien to the usual sounds of his neighborhood. He was pressed to Benny’s back, morning wood tenting the sheet that was the only barrier between them. He didn’t remember falling asleep, but damn, had he needed it. He reached off the bed to grab his pants, looking for his phone. It was just after 5; he had time.

Dean let his head and shoulders drop back onto the pillows and sighed. The enormity of staying the night and everything that had happened hit him like a freight train. Were they dating now? Is that what this was? Did he, Dean Winchester, have a boyfriend? He told himself he was overthinking things, and that Benny was a gentleman, and it didn’t mean anything if they didn’t talk about it.

The things he said came back to him in hi def surround sound. Whatever, it didn’t mean anything if they didn’t talk about it again. No one’s post orgasm declarations should be held against them in the light of day.

Dean closed his eyes and willed himself to fall back asleep. Just as he was close to slipping under, a radio blared to life with ‘Honky Tonk Women’. At least Benny appreciated a good station, Dean thought, groaning to life.

Benny rolled over, and cancelled the alarm before draping his arm over Dean’s stomach. Dean tried not to flinch. To cover up his faux pax, Dean turned to face Benny, leaving a kiss on his forehead.

“You gotta work today?” Dean asked.

“Nah, just figured this is about the time you would have to get up,” Benny told the truth.

“Why didn’t you wake me up last night?” Dean stared into Benny’s sleepy eyes, confused with the lengths of his kindness.

“Bed’s big enough for two, Dean. If I minded you stayin’, I’da said something,” Benny had a knowing glint in his eye.

“You sure?” Dean asked, dropping his chin.

“Definitely. Now, do you want a shower? I can get some coffee goin’,” Benny sat up, which made Dean also.

“Shower sounds amazing, but you don’t have to get up. I can grab something on the way to work,” Dean assured. “I’d hate to think I took away your chance to sleep in.”

“You really don’t let people take care of you, do you?” Benny thought out loud.

“Why? I can take care of myself, no sense bothering anybody.” Dean shrugged, tossing the covers back and rubbing his eyes with the heels of his hands. Benny watched him stretch, the smooth lines of his shoulders shadowed in the fading gray before dawn.

“Alright, well, towels are on the shelf,” Benny said, burrowing back under the comforter.

“Thanks,” Dean whispered before he slowly made it to the attached bathroom.

Once he was cleaned up and half dressed, since he’d left his shirts strewn about the kitchen, Dean sat on Benny’s side of the bed and watched him pretend to sleep. Benny’s mouth hung open and his eyes were just a hair too pinched to be genuine; Dean couldn’t help but smile. “Thanks for last night, Benny. I’ll call you this weekend sometime? Maybe we can do something early next week?”

Benny raised his eyebrows without opening his eyes. “Is that all?”

Dean rolled his eyes and leaned in to kiss Benny’s cheek.

“That’s better.” Benny reached down and squeezed Dean’s knee. “Have a good day.”

Dean kissed him again and walked out of the room.

He stopped to grab donuts and an extra large coffee before heading into the shop. When he arrived, Ellen was already on the phone. But she did a double take when he set down the box of pastries. Her brown eyes told Dean that he was in trouble and he didn’t know if he had enough time to escape before she finished her call.

“We’ll see you Tuesday, Jim, buh-bye,” Ellen wrapped it up. Once the phone was back on the wall she was after him. “Now what in the hell did you get into last night?”

“Nothing, ma’am,” Dean looked at his feet.

“Dean Winchester, don’t you lie to me. Especially not when you walk in here with a hickey on your neck! Now I know it wasn’t Jo that gave you this one, and seeing as you ain’t seventeen no more, I’m not gonna tell Bobby. But, really, Dean?” Ellen tugged at his collar.

Dean’s eyes closed in shame. “Sorry, Ellen.”

“Don’t ‘sorry Ellen’, me. Get in the bathroom, I’ll see if I have something to cover that up. Lord knows we don’t need everyone hooting over you gettin’ some. Friday’s are bad enough keeping everyone working.” Ellen went to the desk and grabbed her purse, rifling through it for her make up bag as Dean positioned himself awkwardly on the toilet seat.

She cocked his head roughly, angling for the best light. She breathed out her annoyance as Dean held his in, worried he’d say the wrong thing and everything would come out. That he’d have to come out.

“Anyone I know?” Ellen asked after she started blotting.

“Probably not?” Dean swallowed.

“Alright, you’re not my shade, but those idiots won’t know that. Get your uniform on before somebody sees you in yesterday’s clothes, you hear me?” Ellen warned.

“Yes, ma’am.” Dean bolted out of the small bathroom like a kid released from time out.

“Oh, and Dean?” Ellen called.

Dean stopped, head dropping in defeat before he turned to face his real boss. “Yeah?”

“Thanks for breakfast.” Ellen grinned wickedly and walked over to the donuts he had left on the back counter.

“You’re welcome. And, uh, thank you, too.” Dean gestured awkwardly to his neck. Ellen nodded and winked.


	5. Cornered

**Summary for the Chapter:**

> No kink square this chapter, just backstory and bowling. Mention of drug use. General flirty banter. xoxo

The crack and rumble of balls striking pins rang throughout the bowling alley; the consistent soundtrack of Dean’s Wednesday nights. He had gotten there early, just after six, to claim their alley and get himself dinner before the rest of the team arrived. Dean shrugged into the simple black and red collared Singer’s Slingers bowling shirt with his name on his left pec. As he sipped his beer and waited for his burger basket, he wondered how late Sam would be this week.

Ash and Bobby showed up just as Dean had a greasy mouthful. He managed to murmur his greetings as they bypassed the bar for the row of vinyl chairs, changing out of their street shoes. They were followed shortly by Mick, who always seemed to swagger in, no matter how ill fitted his bowling shirt. Dean continued to devour his burger and fries as the team ordered their drinks one after the other. It was 6:25 and the other team were toweling off their balls, eyeing them while glancing at their watches. 

“C’mon Sam,” Dean urged under his breath.

“Sam, I expect, but where the hell is Cas?” Bobby wondered, squinting towards the entrance.

“Told you, you should have asked someone else to take the old man’s spot,” Dean smiled smugly, before popping another fry in his mouth.

“Yeah, well, most my friends are too old or too tired for this shit. Can you imagine Rufus out here each week?” Bobby sighed, shaking his head before taking a sip of his whiskey.

“Bobby, can I ask you something?” Dean started. “Are you still bowling because you enjoy it or because it’s a night out of the house?”

“You work with your wife for twenty years and tell me if you wouldn’t be out here every chance you got.” Bobby eyed Dean like he was slow. A burning grin pulled across Dean’s face, he almost choked on his last bite he was laughing so hard. Dean took a swig of his beer and Bobby rolled his eyes.

“Singer! Let’s go!” Roy Wilkinson called from down on the lane.

“What a jackass,” Bobby whispered to Dean, before turning to the opposing team’s captain. “Yeah, I’m getting there.”

It was 6:31.

Dean had learned by now to place Sam last in the line up, but Cas usually went second. With a quick scramble, Dean adjusted their bowling order and sent Cas and Sam their own personalized texts of annoyance. It shouldn’t be that much of a deal, but he was embarrassed. Plus, Dean didn’t want to see Bobby continue to take shit for their tardiness.

At 6:44, a sheepish Castiel and an annoyed Sam walked into the alley together. Sam still had his suit on, his bowling bag slung over his shoulder. 

“Dude, what the hell?” Dean asked once his brother sat down to swap shoes.

“The hoopty bit it, Cas called me because he figured I was closest,” Sam explained, knowing that would have been Dean’s next question.

“Did he hit anybody or did it just die?” Dean asked, eyes raking over Cas’s body for signs of injury.

“It killed while he was driving. Not sure if it’s electrical or if he just ran out of fucking gas,” Sam whispered, frustration evident.

“Well, you guys missed the first frame, but you got yourself a hot minute to catch your breath and grab a beer,” Ash butt in. Mick came back from picking up a spare and the story got told all over again.

“I’m really sorry, Bobby,” Cas explained.

“You bowl for a mechanic’s team, boy. You shouldn’t have let it get that bad in the first place,” Bobby dismissed the clueless man as he made his way to the ball return.

“Dean?” Cas asked, leaning over Dean’s shoulder at the now useless scorer keeper’s spot.

“Yeah?” Dean replied.

“Do you think, could you give me a ride to the bar? And home after I do my nightly paperwork?” Cas explained, his blue eyes beseeching and all too familiar.

Dean groaned and closed his eyes. “How late? I’ve got a day job I need to be at, too, man.”

“Wednesday’s are Ladies’ Night, so it could be awhile,” Cas pondered aloud. “But you don’t have to stay, I can ask at the bar, maybe Ana wouldn’t mind.”

Dean’s stomach instantly knotted with guilt, knowing how the waitress would feel to be trapped with Cas duty after a long shift. He shouldn’t have been so short with him, his car problems probably weren’t his fault. 

“Nah, man, I got you. Let’s just bowl, get out of here as soon as possible,” Dean suggested, chin jutting out toward the lanes. Cas was up.

“You’re a lifesaver,” Cas grinned in relief. Dean swallowed and nodded, biting back the smile that crept up whenever Cas looked at him like that. A sour taste settled in the back of his throat as he watched Cas barely clip the 6 and 10 pins. Ignoring the rest of the frame, Dean went back for another drink before it was his turn.

Losing the first game was inevitable, but the Winchester brothers had a reputation to uphold and they rallied the team for the final two games. Together, they gave the opposing team some much deserved karma. Dean racked seven strikes in a row, but missed the 7 pin on his last ball. Sam, looking utterly ridiculous in his dress shirt and bowling shoes, followed up his tenth frame with a shaky spare. Then he pulled a strike out of thin air with the third ball.

The lane erupted.

Mick and Ash hooted and bumped chests. Dean jumped at his brother, nearly tackling him, before lifting him off the floor by his waist in celebration. Bobby, proud as ever, gave everyone a high five before he shook hands with the now salty Roy. Then Bobby ensured his team followed suit, as a sign of good sportsmanship, even if their faces didn’t hide the smugness of victory.

The champion’s high was short lived for Dean, because reality reared its ugly head when Cas awkwardly started to shadow him as they cleaned up their equipment. Dean towelled off his ball and slipped it into his bag, trying not to let the disappointment of missing out on a drink with the team to cart Cas’s ass across town show. Or the phantom nervousness of being alone with him that Dean had to tell himself to shake.

Cas was just his friend. He had only ever been his friend. No matter how many times Dean craved to be alone with him, it had never meant anything more than friendship to Cas.

Dean had nothing to feel guilty about. But when Cas dropped onto the bench seat beside him in the impala, Dean’s heart started to race. He felt like he was walking a dangerous line between ambiguity and cheating.

“Thanks again, Dean,” Cas’s deep voice croaked.

Plastering on a company smile, Dean brushed him off. “It was only a matter of time for that jalopy anyway, now if you just trust me and sell the damned thing, maybe you could get a reliable set of wheels.”

“Ash says he can have it at the shop by tomorrow afternoon,” Cas threw out there tentatively. 

Dean gave Cas the side eye. “You’re calling Ellen first thing and BEGGING her to work you in, cuz I am no good at weaseling somebody onto the schedule.”

“I know, Bobby warned me. And Ash.”Cas squinted in thought. “And Mick, now that I think about it.” 

Dean told himself to keep his eyes on the road. And to ignore the suddenly crushing weight of his phone against his thigh. He felt like he should be letting Benny know what he was doing, somehow. Like if he didn’t tell Benny where he was and with who, then he was asking to get dumped. 

Dean, no stranger to self-sabotage, overthought until his head hurt. He couldn’t cheat if they weren’t dating. Driving a friend home wasn’t cheating. It didn’t matter that he had had feelings for Cas for as long as he could remember. Benny wasn’t his boyfriend. Officially. Right?

Cas turned to look at Dean. “You’re awfully quiet tonight.”

Again with the inopportune observations.

“Just got a lot on my mind,” Dean dismissed Cas’s concern and leaned over to turn on the radio, close enough that Dean got a whiff of Cas’s familiar cologne. The scent flooded Dean’s senses with bittersweet memories and he had to clear his throat to clear the haze of desire that was always associated with it, with Cas himself. Dean drummed his thumb against the steering wheel and held onto the music for as long as he could.

They arrived at The Pearly Gates just before ten, cars and suvs filled the small parking lot and spilled over onto the narrow side street. Dean cursed and backed into the narrow alley, unwilling to risk his paint job among the other vehicles. 

“Alright, I’ll wait here, go do your busy work.” Dean cranked the car into park.

Cas gave Dean a cautious look before he crawled out of the passenger seat, mindful of the space between the building and his door. Dean didn’t want to think about whatever Cas thought was going on with him. And Dean really didn’t need him prying all of the sudden. 

Dean thought about how oblivious Cas used to be and how much he had changed since they’d been friends. He was still Cas, but he wasn’t the same. 

_ They’d met at a party on campus, which Dean always seemed to find despite not attending. A very drunk Cas had been locked out of his house by his asshole roommates, which were mostly his brother Gabe’s friends. Dean sat on a half-broken picnic table in the backyard toking, as Cas yelled to be let in. It was barely above freezing, but Dean didn’t want to share with the asshole college crowd he’d seen so far._

_ Cas was in black jeans and a tee shirt, shivering.   
_

_ “Hey buddy?” Dean called out. “Look, give me a sec and I’ll pick the lock for ya, alright? Cool it.”_

_ “What?” Cas looked at him like he had three heads._

_ Dean chuckled. “Stop yelling. I’ll get you in. Just let me finish my joint.”_

_ Cas walked over, rubbing his arms with his hands before he started blowing on his hands. Dean had stared, the buzz slowed his thoughts. He just took in the details of Cas’s hands and the way his meaty lips probably looked as the hot air left them. _

_ “You want a hit before I pinch it off?” Dean offered, hand extended in selfish offering._

_ “I’m good.” Cas waved him off, smiling without teeth. A good kid, Dean thought, or a dweeb._

_ Dean sucked in the last puff of smoke and carried it in his chest as he crossed the lawn to the backdoor. As he squatted, he exhaled, letting himself completely relax before he dug for his small set of tools. _

_ “I’m sorry, but my roommates are—,” Cas started._

_ “Dicks?” Dean guessed._

_ Cas sighed in agreement, and that moment Dean probably will never forget as long as he lives. Dean looked up to see Cas in the yellow glow from the porch light, his blue eyes distinguishable for the first time.   
_

_ “Uh?” Cas squinted in confusion._

_ “Right.” Dean sighed and shook his head, fitting the pick into the lock._

_ “You’re sure you can do this?” Cas continued, disbelief clung to every syllable._

_ But Dean didn’t have to answer, because just then Dean cackled in triumph, “Yahtzee!” and the door swung open. _

_ Cas marched past him and into the warmth of the overpacked house. He turned just before he got swallowed by the crowd and nodded his thanks, eyes deep enough for Dean to get lost in._

Dean couldn’t remember much else from that specific party, but meeting Cas. They weren’t friends until a few more chance encounters and a flat tire, but it was their beginning. 

Dean hadn’t told Benny about Cas, other than he was a friend that he helped out. He didn’t have labels for what Cas meant to him, he’d never let it solidify from thought and feeling into word or definition. There had been something there and if he wasn’t careful, Dean could get lost in the familiarity, the lingering hope of perpetual possibility.

Dean probably should say something, eventually.

The car had gotten cold while he waited for Cas to finish the deposit. Dean had turned off the engine to save the gas, but was starting to regret it when his phone rang. 

“Heya, gorgeous, how’d ya bowl?” Benny drawled before Dean could finish his greeting.

“Alright, just around my average, but I tanked the last game. You off work already?” Dean asked, knowing Benny usually worked well past mall hours if he was in the middle of something. 

“Yeah, leaving it for another day. You at home?” Benny continued.

“No, at the bar, killing time,” Dean inaccurately summarized. “Why? You miss me?”

“Well not if you’re gonna be like that, I don’t,” Benny teased.

“What days are you off again?” Dean sidestepped.

“Tomorrow and Sunday. You wanna come over?” Benny asked.

“I do, but I can’t, I’m wiped. Six am is early enough on a good night,” Dean apologized. “I can roll in after my shift at the bar on Saturday though, if you don’t mind me showing up close to three.”

“That could work. I’ve gotta be somewhere at eleven, but you’re welcome to join me,” Benny offered.

“That depends, is it a church service? I need to prepare myself for the smiting showing up after a night with you,” Dean countered.

Benny laughed, “Not a’tall. Me and some buddies do brunch every week.”

Dean sobered up, but he couldn’t stop the snark. “You do brunch?”

“Yeah?” Benny replied, not giving Dean anything more. Dean licked his lips and gaped at the offer. Benny wanted to introduce him to his friends. “You alright, cher?”

“Yeah, just got distracted, sorry,” Dean lied horribly. “I don’t want to crash your plans. We’ll see, alright?”

Benny inhaled audibly. “Yeah, I understand. You’ll still stay over though?”

“Yeah, I’ll be there.” Dean agreed.

“Hey, maybe, if you don’t mind I could slip in for a drink after my shift Friday?” Benny suggested.

Dean smiled. “That’d be great. Gives me something to look forward to on a double shift.”

“You alright?” Benny almost whispered.

“Yeah, just tired, sorry, not my usual charismatic self,” Dean huffed.

“Nothing to be sorry for, sugar. Just checkin’ in on ya,” Benny soothed. Dean closed his eyes and relished in the sound of Benny’s calming voice.

“Tell me something,” Dean asked, not wanting to end the conversation.

“What do you want to know?” Benny chuckled, deep and genuine.

“I don’t know, just keep talking. What were you working on tonight?” Dean said.

“A pair of saddle bags for a custom bike,” Benny started. “Real nice ones too. Sturdy, but soft. Got some staining to do then the branding. But I got everything cut and measured for now. You ride?”

Dean hummed, then remembered he was asked a question. “Sorry, on occasion, I don’t have a bike of my own anymore. Do you?”

“Well, they don’t call me a leather daddy just for my outfits, cher,” Benny teased. “Before it snows, I’ll see if we can get the bike out for a spin.”

“Now I’ve got that visual burning through my thoughts,” Dean murmured suggestively. 

“Happy to oblige,” Benny goads. 

“I’m sure you would,” Dean huffs. “Thanks, it was just nice to hear your voice.”

“Anytime, Dean, all you have to do is call. You know that right?” Benny pressed.

“Yeah, I know, I know.” Dean agreed, when an extra blast of cold air hit his side. Cas was back. “I better go. I’ll see you soon.”

“Dean?” Cas interrupted.

“Okay, well, enjoy the bar,” Benny sounded like he’d heard Cas. “Bye, darlin’.”

“Night,” Dean ended the call.

“Who was that?” Cas asked, tugging at his trenchcoat to get the seatbelt on.


	6. Loose Lips Sink Ships

**Summary for the Chapter:**

> Featuring: Dean Winchester/ Benny LaFitte
> 
> Other characters: Bobby Singer, Gordon, Rufus, Lee, with Cas, Sam and Ellen mentioned.
> 
> Written for: @thoughtslikeaminefield and @spnkinkbingo
> 
> Square Filled: Rimming
> 
> Summary: Dean stays over at Benny’s, but can he take the steps to being public about their relationship? What if his worlds collide?
> 
> Warnings: 18+ only. Showering together, generous Dean, handjobs, ball sucking, quality oral sex, analingus, anal play, masturbation, cum play, cum eating, allusion to BDSM equipment, and minor homophobic slurs.

  


  


Dean stumbled into the shower painfully early on Sunday morning. The water was already hot, where it could reach him around the wall that was Benny. He didn’t speak, still half asleep. Instead, Dean nodded and placed a quick kiss to Benny’s lips before taking the soap to lather himself up. 

Benny grinned, eyes bright as ever. Dean could barely keep his open, which made Benny’s body shake with a silent chuckle.

“Yeah, yeah,” Dean grumbled. “Man, I’m already looking forward to the nap I’m gonna have when I get home.”

“Why didn’t you stay in bed? You only got a few hours,” Benny nudged, slipping behind Dean so he could get the bulk of the spray now that Benny was finished.

“Habit. ‘M always up this early. Why I hate workin’ at the bar.” Dean hummed as Benny left a kiss on the back of his neck.

“And why do you do it again?” Benny teased.

“Yeah, yeah,” Dean sighed. He had told Benny about Cas in the afterglow the night before. A pillowcase confession that had Dean crawling out of his skin to put words to things that he had buried for so long. But Benny just listened, which was more than Dean could have hoped for.

“Look, I know he’s your buddy, but sometimes there’s a favor and then there’s gettin’ used,” Benny murmured. “If you ask me? You deserve more sleep.”

Dean grunted as Benny reached around his body and shut off the water; a thick wrist brushed against Dean’s half hard cock. Dean reached behind his back and held Benny’s neck, holding him close. Benny quickly reciprocated and gripped Dean tight. Benny’s breath was hot on Dean’s chilling flesh, the cool air of the attic bathroom catching up as the steam dissipated.

Benny rutted into the cleft of Dean’s cheeks, his balls heavy and teasing against the meeting of Dean’s thighs. Dean’s skin prickled, he leaned back and turned to take Benny’s mouth in a sloppy side kiss. Benny moaned into his mouth and Dean lapped it up. 

Benny broke the kiss, nuzzling his nose with Dean’s. “Let’s get dry, yeah?”

Benny cupped Dean in promise and stepped out of the tub.

They dried off in a rush, smirking, pinching, kissing and groping along the way. Dean maneuvered Benny onto the bed, taking control by denying Benny from continuing to jack him off. Dean centered himself over Benny, hips wiggling to spread Benny’s thighs. Dean’s lips sank down Benny’s throat. 

“What are you up to, hm?” Benny purred.

“Don’t worry about me.” Dean eyed Benny from the curtain of his lashes. “Just lay back and relax, Christ.”

Dean nipped at Benny’s shoulder, and sank lower to drag his tongue over Benny’s left nipple. Benny crossed his hands behind his head and took in the view. Dean’s pink lips costing down his torso, soft, yet forceful. Benny hummed in satisfaction as Dean continued south, calloused hands firm yet tender alongside his hot and searching mouth.

Dean casually stroked Benny with one hand as he left love bites in patches across Benny’s thighs. The sound of Benny’s sighs was the only high Dean wanted to chase. He lapped at Benny’s sack, sucking one side and then the other with indulgent skill.

Benny groaned as Dean dropped down, spreading Benny’s thick thighs back and wide, giving Dean access to his target. Dean circled the tight hole with the tip of his tongue, softer than Benny thought possible. Benny bucked against the tickle, but submitted once Dean’s lips pulled on the sensitive skin just behind his balls. Benny could feel Dean’s smug smirk as his grip tightened on Benny’s drooling cock.

“That’s it sugar, give me some tongue, hm?” Benny purred, reaching down to stroke the top of Dean’s head. Dean obliged, starting with broad strokes of the hot, wet muscle before working it inside. Benny quivered at the sensation, thighs tight as the pleasure surged through him. He slid Dean’s hand away from his dick, taking over so Dean could more thoroughly work him open.

Dean nipped and sucked and tongue fucked Benny’s hole until Benny was moaning out a chorus of praise strangled curses. But Dean wasn’t done yet. He mouthed back up to Benny’s balls as he started to thrust two rough fingers into his now spit laced channel. Dean hummed around the salty flesh, tongue prodding in time with his fingers, overwhelming Benny’s body with pulses of ecstasy. 

Benny cried out, “oh God, Dean! Fuck!”

Dean didn’t stop. 

Benny whined as Dean sucked hard on his taint, thrusting hard against the pinching tension around his fingers. As Benny relaxed, spent and sloppy, Dean slowed his movements. He started by softening his kisses over every inch of Benny’s flesh, leaving a slight lick and a plump dollop of lips as he went. He eased his fingers out carefully, watching Benny for any sign of discomfort.

Hunched over, Benny panted. His blues eyes, hooded with tiring bliss, lingered on Dean as he took his time. 

Dean smiled in his eyes and it made Benny shake his head in surrender, he was no match for such beauty. Dean slinked forward, nuzzling against Benny’s softening cock before he licked it clean. Then he lapped up the remaining spendings over Benny’s belly. Lastly, Dean took Benny’s palm and kissed it, finding it already wiped clear on the sheets.

“Mornin’,” Benny murmured as Dean dropped to his side, belly down, chin resting on his fist.

“Figured you could stand not to get dirty all over again,” Dean explained, lacing Benny’s fingers with his.

“I appreciate that,” Benny cooed, flirting eyes never ceasing to draw Dean in.

“Good.” Dean played it up with a considering pout. Benny chuckled.

“What?! It was a good one, you need more than that?” Benny teased, pulling Dean up to him by their joined hands. “You want me to tell you how good it felt to have you eat my ass or how hot that mouth felt nearly sucking my balls clear off? Hm? That what you need to hear?”

Dean blushed, looking down at their flush chests. “No, it’s just, I dunno.”

Benny leaned up, nudging Dean’s face, so they were breathing the same air, both pairs of eyes searching for something. “Cher, aint nobody come that hard and not enjoy themselves. Stop doubtin’ yourself. You do me good.”

Dean didn’t bother answering, he just kissed Benny hard and quick, too pleased to do anything but smile and sigh. 

“Well, alright then. I better be gettin’ dressed,” Benny apologized. “I suppose you could too, if you must.”

“Yeah, yeah,” Dean brushed the compliment aside and found his clothes from the night before.

Benny slipped into jeans and chaps, before finding a fitted tee and a matching vest. Dean couldn’t help but watch Benny as he finished getting ready for his weekly meet up. From his boots, to his hair, which he covered in a cap, to his intoxicating cologne, and up to him brushing his teeth, Dean stared, disheveled on the bed, unconcerned he hadn’t bothered with such rituals himself.

When Benny was finished, primped and as handsome as ever, he took one look at Dean’s state and cocked an eyebrow.

“That’s what that was about, huh? You’re not coming along, are ya?” Benny asked, disappointment dwarfed by the cool, casual observation. Dean didn’t know how he had become such an open book, but maybe it was just for Benny. Or maybe Benny was just one of the few people who could read his language, understand and appreciate it.

“I wouldn’t know what to do with myself. I’m just—,” Dean tried to explain.

“You’re not ready, I hear ya. But you’re missin’ one hell of a meal,” Benny teased, temptation glinting in his eyes.

Dean stood and stretched. He groaned, mouth watering at the thought of bacon and skillets overly flowing with eggs and potatoes. “Maybe next time.”

“I’m gonna hold you to that,” Benny dropped his chin, making Dean accept the promise of more invitations. Dean rolled his eyes and nodded. Benny smirked and pulled Dean close, rubbing his bearded cheek against Dean’s stubble. “Go on, get home, get that nap in. I’ll call ya later.”

It was a slow day at the shop, a few oil changes and two different patched tires made up most of Dean’s day. Rufus had taken the lone walk in with an unknown rattle, not letting the younger men help as he diagnosed the problem. Gordon made a joke under his breath at that, but Dean knew better than to laugh out loud.

By lunchtime Dean was phoning it in, going through the motions without paying much attention. Sam had been weird at Sunday dinner and it had been bothering Dean since. He figured he was going to have to weasel whatever it was out of Sam that night at the alley, either between frames or afterwards with a few drinks. He wasn’t looking forward to it, but he couldn’t stand knowing something was bothering Sam without knowing how to fix it for him.

Dean grabbed a couple sticks of beef jerky from the vending machine in the lobby and worked through his break, too distracted to need an hour away from work anyway. It was just before one when he heard him. A simple ‘well, well, well’ was Benny’s greeting.

Dean spun on the spot, shock and awe raising the hair on the back of his neck. Which was quickly followed by fear and panic.

“What– what are you doing here?” Dean couldn’t help the shy smile that crossed his face. Stuffed under both of Benny’s arms was a black leather saddle bag, the awkwardness helped Dean to keep his hands to himself.

“Special delivery for one of your co-workers,” Benny shrugged, gesturing to his wares. Then his voice dropped, “Don’t worry, I won’t be long.”

Benny winked.

Dean nodded, trying to play cool. “So I’m guessing those are Lee’s?”

“Yes, sir.”

Dean looked around the lot and back to the office before replying. “Well, I don’t think he’s back from lunch yet. You want to leave ‘em inside?”

“I can wait, he knows to expect me,” Benny said, tone light.

Dean cocked his eyebrow in question and Benny just chuckled.

“So, this is your day job, huh?” Benny surmised, taking in the state of the place.

“Yeah, owners are good friends of the folks, known ‘em my whole life,” Dean explained, hands on his hips. The forbiddenness of Benny’s presence was tight in his chest, talking to Benny had always been easy, but he couldn’t be that Dean here.

“That so?” Benny considered. “Bet they’ve got loads of dirt on you.”

Dean shook his head and smirked. “Probably not as much as you’d think.”

“Don’t you start the innocent act with me,” Benny teased.

“I’m not claiming innocence, just that I was good at not getting caught,” Dean clicked his tongue.

“Yeah, that sounds about right,” Benny conceded. Dean rolled his eyes and shook his head, body itching to be closer. 

“Can I see ‘em?” Dean gestured to the dark leather under Benny’s left arm, stepping inside Benny’s space. Benny pulled out the bag, presenting it for Dean’s inspection. Dean kept his eyes down, dragging over the precision and craftsmanship, careful not to touch, not wanting to soil the unblemished hide.

“Dean, what’s up?” Bobby’s voice broke into Dean’s tenuous bubble of safety.

“Bobby! Hey! This here is Benny. He’s just dropping off some things for Lee’s new baby,” Dean explained, stepping farther away from Benny than was necessary. Bobby eyed Dean’s cagey behavior before leaning out to shake Benny’s hand. Which Benny managed by tossing the other bag under his left arm.

“Nice to meet ya,” Bobby said, appreciating Benny’s firm grip. 

“Pleasure,” Benny agreed.

“I see Lee’s been burning through his overtime again, those sure are sharp though,” Bobby added, appreciating quality when he sees it. “You do these yourself?”

“Yes, sir,” Benny said. “I work out of a storefront at the mall for the most part, but I do a lot of custom stuff on the side as well.”

Dean’s mind wandered and he felt his cheeks grow hot, he knew exactly what sort of things Benny made on the side. Things that could be ordered discretely from an online shop with a different name and sent safely from a P.O. Box in simple, unmarked packages.

“That’s how I know Dean, here,” Benny explained. “He picked up a jacket from me a month or two back.”

“Well, my apologies then, having two of these knuckleheads for customers can’t be easy,” Bobby teased. “They work for me and I can’t deal with ‘em most the time.”

Benny chuckled. “Could always be worse.”

“Don’t I know it,” Bobby huffed. “Well, I got a carburetor I’m pulling out of a junker waiting for me. Have a good one.”

“You too, take care Mr. Singer,” Benny tipped his cap as Bobby sauntered off to the yard.

“You goin’ for brown noser? ‘Mr. Singer’?” Dean hissed, trying not to get too loud.

“I like to make a good impression,” Benny shrugged. “Lee late a lot?”

Dean weighed his hand, and curled his lip, a clear ‘half the time.’

“Figures,” Benny sighed. “If I leave these here, can you get the money from him? He still owes me half.”

“Uh?” Dean scratched the back of his head and considered. “S-sure, I guess.”

“Look, I don’t want to put you in a bind, but I’ve got a fitting coming at 1:30,” Benny explained.

“No, it’s fine. I’ll just say I’m headed that way or something,” Dean assured, knowing the mall and the bowling alley were in different directions. “Could use a new bowling bag anyway.”

Benny nodded, letting Dean work out his story. He carefully handed over the merchandise once Dean had wiped off his hands. Then said, conspiratorially, “thanks, brother.”

Dean shook his head and gave Benny the slightest air kiss, which made Benny cover his heart in shock and affection. Dean grunted, “get goin’, I’ll get you that money when I can.”

“I’ll be seein’ ya,” Benny winked and strolled over to his old pick up. Dean adjusted the bags in his arms and watched Benny climb into the truck and drive away. He hoped Benny wasn’t late for his appointment.

The loud roar of Lee’s chopper preceded him into the parking lot fifteen minutes later. Dean had Ellen store the saddlebags on some spare shelving near the office so he could get back to work. Idle hands were never good things for Dean to have, and after having Benny meet Bobby and in more of his personal spaces Dean needed to focus on something other than his spiraling thoughts.

Dean waited until Lee was inside the garage to call out to him, “got your special delivery! Ellen’s holding them hostage for now.”

Lee’s eyes lit up. “Sorry I missed him, I had to run to an atm once I remembered.”

“It’s fine, I’m heading that way after work, said I can drop it off for you, if you want.” Dean shrugged, trying to remain casual.

“You know Benny?” Lee asked, surprised.

“Yeah, man, where’d you think I got my jacket?” Dean folded his arms over his chest and leaned back against the rusting Caddy he was working on.

Lee paused and looked at Dean suspiciously. “Yeah, Benny’s good at what he does, isn’t he? Had him do all our vests a year or so ago.”

Dean nodded. “Good shit.”

“Yeah, he does some badass leatherwork for a fairy,” Lee poked into Dean’s nonchalance. He gave Lee a questioning look perhaps a second too late. “Yeah, dude’s a flamer.”

“‘Kay.” Dean was not up for this. “Can I just get what you owe the guy? I don’t need his life story to get a deal on a bowling bag, man.”

Lee looked over to Gordon who had been eying the conversation like a bloodhound. “Of course, just figured I’d warn ya.”

Lee reached into his back pocket and counted out the twenties until he had enough, he folded them in half and slapped them into Dean’s outstretched palm. Dean gave him a not so appreciative smile. “Pleasure doing business with you.”

“Whatever,” Lee mumbled and stomped off to claim his gear.

Dean counted the cash, once Lee was out of sight. After he tucked it into his money clip, Dean rolled his neck. “Gordy! Turn it up, let’s get this piece of shit out of here already.”

Gordon smirked and cranked the radio, then everyone got back to work.

  



End file.
